Over the last 20 years I’ve lived, worked and holidayed in the Italian regions of Tuscany, Umbria and Le Marche. As people often ask me about family holidays to Italy, I’ve put together this sample 14 day Italy itinerary which takes in both iconic sites and lesser known gems. Highlights of this family holiday to Italy include the Leaning Tower of Pisa, Tuscan wine tasting, peaceful hilltop towns in Umbria and a stunning drive through the Sibillini Mountains to the underrated sandy beaches of the Adriatic coast in Le Marche. A family holiday to Italy has all the ingredients for a great summer road trip. This itinerary can be modified to take in different attractions, depending on the age of your children.
Accommodation in Italy
Aside from a city centre hotel or apartment in Pisa for your first few nights, I’d recommend staying on farms for the rest of this family holiday to Italy. At an agriturismo (Italian farm stay) you can expect simple, good value rooms or self catering apartments along with excellent home-cooked food, a swimming pool and plenty of space for children to run around. There’s often a play area for little ones and that all important WiFi for teens. I have always found the hospitality to be exceptionally good at agriturismos and I love the idea of enjoying long al fresco evening meals while the children play outside with new friends.
Is a family holiday to Italy complete without a trip to Pisa? Ensure you stay a night or two: visit the tower at dusk or dawn, when the crowds have thinned. The Piazza dei Miracoli is a magical place: although kids will be drawn to the tower, make time to wander through the cathedral and the baptistry which are both packed with incredible frescoes and sculptures. You can promise the children an extra large gelato if they agree to a quick art history lesson.
If you’re travelling to Pisa with pre-schoolers, the Luminara di San Ranieri on the evening of 16th June is stunning; every window in the city is lit up by candles. The festival is an incredible display which takes Pisan residents most of the day to set up.
But every evening in Pisa is lovely. Join locals for a wander along the River Arno, stop for an ice cream at Bottega del Gelato by the central bridge of Ponte di Mezzo, before heading down Corso Italia for some evening retail therapy (shops are open until 8pm). Visitors who claim to have had an underwhelming experience in Pisa have obviously not enjoyed an evening passeggiata through this lovely city.
Where to stay in Pisa
I was lucky enough to live on the River Arno during my stay in Pisa. And that’s where I’d recommend visitors stay too. It’s far enough away from the Tower for restaurants to be priced for locals and students rather than tourists and you’re near to the station for trips out of the city. Apartments are perfect for families. Palazzo Kinsky on via San Martino is in a good location a block from the river and gives visitors a taste of palazzo life while Art Apartment on my old street Lungarno Galileo Galilei offers a more contemporary stay.
Lucca and Viareggio
Pisa is a great base for exploring other family-friendly parts of Tuscany. There are regular trains to seaside Viareggio (20 minutes) where you can hire bikes and safely cycle along the seafront. Inland, Pisa is a 30 minute train journey to delightful Lucca. Perfect for small children, Lucca features huge city walls which can be walked or biked along, there are play areas next to the walls as well. The city’s Piazza dell’Anfiteatro is a good place to break for lunch while a climb up tree-topped Torre Guinigi will burn off that tiramisu and/or the gelato you’ve indulged in.
Families with older children might prefer a visit to Florence for a dose of Renaissance art and history, it’s just an hour from Pisa by train. If you have just a day in Florence, it’s advisable to book tickets to the Uffizi Gallery online in advance so that you’re not forced to join the snaking queue around the building. The Uffizi is one of those pleasing galleries where you come across a world famous work of art each time you turn a corner. Highlights include Botticelli’s Birth of Venus and Titian’s Venus of Urbino. Young children will no doubt enjoy studying Caravaggio’s Medusa with its twisting snakes.
If you and your family are keen art historians, once you’ve marvelled at Florence’s cathedral and bell tower and walked across the Ponte Vecchio, it’s worth seeking out one of two of the city’s lesser known gems. I’d recommend a trip to the Brancacci Chapel at the Church of Santa Maria del Carmine where you’ll find some of the most significant frescoes of the early Renaissance: Masaccio’s Life of St Peter. If you’ve ever stood shoulder to shoulder with hundreds of other tourists in the Sistine Chapel in Rome you’ll be relieved to discover that the Brancacci Chapel operates a reservation system with a maximum of 30 visitors at a time.
If you prefer your sightseeing to be of the more natural variety, hop in a rental car and head north from Pisa into the Apuan Alps, a place I have very happy memories of from my time as a student at Pisa university. I spent weekends rock climbing in the Apuan Alps but you’ll find hikes of varying lengths, peaceful villages and hamlets such as those of Stazzema, and all amid stunning mountain scenery.
Montepulciano and the Val d’Orcia
Once you’ve had your fill of Pisan hospitality, it’s time to travel south. There are endless enchanting places to visit in Tuscany, one of my favourite spots is the diminutive town of Montepulciano where you can enjoy a few glasses of Vino Nobile. Not to be confused with Montepulciano d’Abruzzo, the wine of Tuscan Montepulciano is made primarily with the Sangiovese grape (also used in Chianti wines) and tastes delicious with some Tuscan steak at an agriturismo. When you holiday with children it’s important to remember that you, the grown ups, are on holiday too. So, visit a few vineyards, savour some of that delicious wine and let your children entertain themselves.
If you’re travelling from Pisa to Montepulciano, you’ll find the popular towns of Volterra and San Gimignano are handily on route. They’ll both be busy in the summer months but with good reason, they really are delightful and make the perfect stop for lunch.
If you base yourselves near Montepulciano for a few nights, you’re within easy reach of Siena but also some smaller and lesser-visited parts of Tuscany such as Pienza (used in the filming of the English Patient) and Radicofani. These towns are part of the UNESCO-listed Val d’Orcia region: think rolling hills and cyprus tree-lined lanes, it’s that landscape. Head for hilltop Montichiello for a proper hit of quintessential Tuscany. Also nearby is San Casciano dei Bagni, where you can soak in the thermal waters of ancient Roman baths which are remarkably free to access and remain off the radar to most tourists.
Where to stay near Montepulciano
Alas, I don’t actually remember the name of the agriturismo I stayed at during my last visit to Montepulciano. However, I think Agriturismo Nobile looks like a particularly good option for a family holiday in Tuscany: apartments and hotel rooms, a restaurant, swimming pool, bikes for hire and a play area. It also offers a shuttle service into Montepulciano if you want to head out for dinner.
If you’re considering a trip to Tuscany with teenagers, I’ve included a trip to Pistoia and the island of Elba in my post about holidaying with teens.
Assisi and Spello
As you head east on your holiday to Italy, you’ll encounter fewer and fewer tourists until you reach coastal Le Marche where, in August, you’ll be hard pushed to find anyone not speaking Italian. But first let’s talk about Umbria. You wouldn’t expect a land-locked region to be a holiday hit with kids but there are plenty of fun things to do in Umbria with children including touring a chocolate factory and climbing medieval castles, plus there are several great places to swim.
From Montepulciano in Tuscany I’d recommend driving across to tiny hilltop Panicale for a morning coffee before continuing on to Assisi for lunch and some essential sightseeing. If your children baulk at the thought of more frescoes (Assisi’s Basilica of Saint Francis houses important works attributed to Giotto), you can bribe them with the promise of scaling Rocca Magiore, Assisi’s 14th century fortress. which offers great views from the top.
Near to Assisi you’ll find lovely Spello, a picture perfect honey-stone village which is the perfect retreat for a peaceful afternoon’s wander and maybe a gelato…
If you need time-out from art and history (and tons of tourists: Assisi is very popular), you might prefer to take the kids to Lake Trasimeno where you can while away your afternoon climbing the ramparts of Rocca del Leone at Castiglione del Lago or hop in a pedalo to burn off some of those ice creams.
Wherever you choose to spend your first day in Umbria, consider using Gubbio in the north of the region as your base. This medieval town clings to the steep slopes of Monte Ingino. You can make the most of the impressive views over the Chiascio Valley below by taking the rather ancient looking cable car to the summit of the mountain, if you suffer from vertigo you might prefer to enjoy a coffee at one of the cafes instead. Nearby is tiny hilltop Montone and the elegant town of Citta di Castello.
From Gubbio, you’re within day trip distance of many of central Italy’s highlights. You could trace Umbria’s history through the impressive architecture of its capital, Perugia, where you’ll find Etruscan arches leading you into medieval alleyways. Your children might prefer the Perugina chocolate factory (home of Baci chocolates) which offers tours in English. If you’re travelling with pre-schoolers or post-exam teens, try to time your stay around the annual Umbria Jazz Festival (early July) which features day time and evening concerts, many of which are held in Perugia’s piazzas and don’t cost a penny. Don’t expect overly authentic “jazz”, it’s more about the live music experience!
Just to the west of Perugia is Citta della Domenica. I’ve yet to visit this Disney-esque theme park but I’ve heard it’s popular with small children: apparently you’ll come across Snow White, Sleeping Beauty and Pinocchio plus there’s a steam train and petting zoo. If you fancy something a little more grown up (well, a lot more grown up), pay a visit to Montefalco. Known as the balcony of Umbria due to its impressive views over the valleys below, Montefalco is home to the Sagrantino grape which makes a particularly delicious red wine. Perhaps bribe your children with a trip to Citta della Domenica in exchange for a visit to a few vineyards in this unmissable part of Umbria. Lunch in the town should also be on your list.
Where to stay in Umbria
Palazzo Gastaldo, near Gubbio
As agriturismos go, this has to be one of the best I’ve visited. Hidden away on top of a hill, reached via what seems like a never-ending track, this property is worth the drive. Palazzo Gastaldo features a collection of very old, rustic apartments with beautiful traditional furniture, I know my kids would love La Torre: a series of rooms reached via a very steep staircase with a little terrace at the very top (not recommended for those who need the loo in the middle of the night or indeed for anyone interested in health and safety!). Staying here is a bit like staying in a history book. There’s a swimming pool and a restaurant, great views and gardens that children will love exploring.
Agriturismo Sant’Illuminato, near Citta di Castello
This is a great option in Umbria for families. It’s located near Citta di Castello within day trip distance of Perugia, Assisi and Lake Trasimeno. Sant’Illuminato features a collection of apartments surrounded by huge amounts of green space for children to burn off energy. There’s a swimming pool and small play area as well as a restaurant: all the ingredients for a holiday in Umbria with kids!
Le Silve di Armenzano, near Assisi
I absolutely love the location of this hotel. As with Palazzo Gastaldo, it’s reached by a long track up a mountainside and when you reach the top, you’re in the middle of the countryside with nothing but forests and hills around you, it’s breathtaking. The rooms are good value and the classic rooms in the main building are wonderfully characterful with dark wooden beams and thick stone walls. There are also some self catering apartments away from the main building which offer particularly good value for money.
Palazzo Seneca, Norcia
If you’d like to linger in Norcia (see below) before heading over the border into neighbouring Le Marche, this is the place to stay. I visited before the 2016 earthquake but I hear the hotel is fighting fit and welcoming guests once again. Expect incredible views and incredible food.
Urbino and the Frasassi Caves
Fans of Umbria might point you in the direction of delightful Todi, rather than Gubbio, as your base for exploring the region. From there you’re within easy reach of Orvieto and Spoleto, both excellent towns to visit in Italy with kids. However, from Gubbio you can nip over the border into northern Le Marche to visit one of my favourite Italian cities: Urbino. I’ve visited Urbino, birthplace of Renaissance painter Raphael, in the middle of August and despite the city’s historical significance, it draws just a handful of tourists. There are paintings by Raphael, Titian and many other masters in the town’s 15th century Palazzo Ducale and you can also visit Raphael’s childhood home. However, my favourite thing to do in Urbino is take a summer evening’s wander through the town, with a gelato.
Also accessible from Gubbio is the Frasassi Cave complex in Le Marche. This is a great escape from the heat: it includes Europe’s largest single cavern, Grotta Grande del Vento which is big enough to swallow up Milan cathedral.
Drive from Norcia to Ascoli Piceno
Not everyone would put the words “enjoyable” and “driving” in the same sentence as “Italy” but it’s good to dispel the odd myth now and again so here goes… One of the most enjoyable driving experiences I have had was in Italy. Set off early from your base in Umbria and head to Norcia, a town famed for its pork produce: stock up on piggy goodies from one of the norcinerias (pork butchers) and then head off, with your paper map I might add, in the direction of Castelluccio. You’ll be on the narrow zigzagging SP477 which takes you through the stunning Piano Grande. This is a place of vast meadows with incredible wild flowers in early summer, surrounded by the peaks of the Sibillini Mountains. Castelluccio is in a lonely but dramatic spot on top of a hill overlooking this grand spectacle.
Norcia and (especially) Castelluccio were badly affected by the earthquake which hit central Italy in 2016, all the more reason to pay this area a visit and help the recovering economy. Aside from the pork products, this is the region for truffles and lentils so if you’re not one for picnics be sure to sample some local delicacies in one of the local restaurants.
Sibillini Mountains National Park
If you’re keen on hiking and have older children, you might prefer to pass on the art and history of Umbria and Le Marche and concentrate your energies on the regions’ natural beauty instead. There are walks of varying lengths in the Sibillini Mountains. Norcia in Umbria or Amandola in Le Marche are good bases for exploring the national park. On my next visit to this region I’m determined to visit Lake Fiastra with its sandy beaches and crystal clear aqua marine waters. It makes a great alternative to visiting the Adriatic coast.
However, if you’d prefer to just drive through the Sibillini Mountains, it does make for a magical day out: I’ve driven from Norcia to Ascoli Piceno (or vice versa) a couple of times, at different times of year and the roads have always been fairly quiet.
Ascoli Piceno and around
Packed with pretty hilltop towns to rival those of Tuscany and Umbria, but devoid of tourists: that is the beauty of Le Marche. There are plenty of villas at more affordable prices than in the other central Italian regions but if you’re only staying for a few days, an agriturismo works best.
If you’ve managed to incorporate a visit to Urbino from Gubbio as suggested above, I’d recommend basing yourselves a little further south for your final stop on this itinerary: between Ascoli Piceno and the coast. Ascoli deserves a visit for its wonderful Piazza del Popolo: perfect for a long lunch. If you have kids in tow, fear not, the piazza is car free and big enough to absorb their squeals while you soak up everything else. Make sure you try the stuffed deep fried olives, a delicious local delicacy!
We enjoyed a week staying at a villa on our last Family holiday to Italy, near the tiny hilltop town of Montedinove. From there we explored the lace making town of Offida and visited the lovely family-friendly beaches at Grottammare. I’d definitely recommend staying slightly inland when you visit Le Marche: it can be pretty hot and busy down at the coast whereas the hilltops have a refreshing breeze even in the height of summer. The rolling farmland is backed by impressive mountain ranges so you’re guaranteed a mesmerising sunset every night.
Seaside Le Marche
A family holiday to Italy isn’t complete without a few days at the seaside. The beaches of Le Marche are a total immersion into authentic Italian life. Don’t come for glorious coastal scenery (although the Parco del Conero does offer this in the north of the region). In Le Marche you’ll experience a proper Italian beach holiday: families and friends taking their passeggiata through the shallows of the Adriatic, thriving bars and restaurants (if you come in August), tons of kids gambolling across the sand. It’s great fun. On our last visit to Le Marche, we loved our daily trips to Grottammare.
Where to stay in Le Marche
Agriturismo Ramuse, near
I’ll admit that I haven’t visited this property but it is very close to Montedinove so I can vouch for its great location. This is a good option if your budget can’t stretch to the price of a villa but you would like the option to self cater. There are 4 bedrooms here plus a two bedroom suite with a small kitchen. There’s also a swimming pool and a restaurant.
Villa Cicchi near Ascoli Piceno
This is a small charming and characterful hotel just outside Ascoli Piceno. Expect delicious food and wine, informal service and a lovely pool to relax by after a day of sightseeing. I stayed here pre-kids, I’d probably wait until my children are a bit older before returning as it has quite an intimate vibe.
Villa Ulissi near Montedinove
We spent a wonderful week in this villa with some friends. It has incredible views of the hills and mountains but it’s close enough to the coast for days at the beach. I highly recommend this property!
Camping Village Internazionale near Sirolo
I’ll admit that I’ve only seen this campsite from a distance but it is in such a brilliant position close to so many great beaches in the northern part of Le Marche that I am confident it would be a great option.
Tenuta le Piane, near Amandola
This is a collection of proper rustic apartments hidden away from the modern world. It is incredibly peaceful at Tenuta le Piane: there are no busy roads near by, just mountains and meadows. The accommodation is traditional: don’t expect anything luxurious as it is a very authentic place to stay. Children love it: there’s a pool and bikes to borrow and lots of space to run around including plenty of shady areas.
Hotel Emilia, near Ancona
If you’re after something a bit different and you have a bit of money to spend, the Emilia is an art hotel on a clifftop with incredible views of the turquoise Portonovo Bay below. It’s family friendly too and there’s a big swimming pool.
Travelling to and from Italy
Start your family holiday to Italy by flying into Pisa on the east coast. If you’re returning to the UK from Le Marche, there are Ryanair flights from Ancona and over the border at Pescara in Abruzzo. However, unless you live near Stansted in the UK, these little airports won’t be much use so end your trip with an epic drive to Rome through the mountainous Gran Sasso National Park in neighbouring Abruzzo. If you opt for this route, you’ll be following the ancient Via Salaria, a Roman road which carried salt from the Adriatic to Rome.
And if you have a night to spare at the end of your family holiday to Italy, consider an evening in Frascati, a relaxing summer escape for Romans and others in the know.
Suggested family holiday to Italy 14 night itinerary
Arrive into Pisa
The airport is really close to the city so hop in a taxi (or take the 8 minute train journey)
3 nights in Pisa in a central hotel
Visits could include Viareggio, Lucca and Florence
Pick up a hire car and drive to Montepulciano (3 hours), perhaps stopping in Volterra or San Gimignano for lunch
3 nights near Montepulciano in an agriturismo
Visits might include Siena, Pienza and Radicofani
Drive to Gubbio (2 hours), perhaps stopping in tiny medieval Panicale and Assisi or Lake Trasimeno
4 nights near Gubbio in an agriturismo
Visits could include Perugia, Urbino, Asissi and Spello
Drive to Le Marche via the Sibillini Mountains with a stop in Norcia to pick up a picnic lunch (4 hours)
4 night in an agriturimo near Ascoli Piceno
Visits might include Ascoli Piceno, Offida and Fermo or the seaside towns of Grottammare and San Benedetto del Tronto
Drive to Rome via the Gran Sasso National Park (3 hours)
We stopped for lunch at the little mountain town of Antrodoco on the border of Abruzzo and Lazio
Disclaimer: This post contains affiliate links. Should you click to purchase, it is at no additional cost to you, although I receive a small commission that goes towards the running of this blog.
Pin for later:
Have you taken a family holiday to Italy? Let me know in the comments below.